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#$Date: 2016-03-21 19:10:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178838 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/92/4109225.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4109225
loop_
_publ_author_name
'Chandra Shekhar Purohit'
'Sandeep Verma'
_publ_section_title
;
 Patterned Deposition of a Mixed-Coordination Adenine-Silver Helicate,
 Containing a π-Stacked Metallacycle, on a Graphite Surface
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3488
_journal_page_last               3489
_journal_paper_doi               10.1021/ja068892b
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C16 H21 Ag2 N13 O6'
_chemical_formula_sum            'C16 H21 Ag2 N13 O6'
_chemical_formula_weight         707.20
_chemical_name_common            '9-ally adenine AgNO3 salt at pH 8.3'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5313(7)
_cell_length_b                   16.3368(9)
_cell_length_c                   13.0762(8)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.0
_cell_volume                     2445.2(3)
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND 3.1 d'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'Phi-Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15882
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        <0.05
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  0.8128
_exptl_absorpt_correction_T_min  0.7321
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.084
_refine_diff_density_min         -1.520
_refine_diff_density_rms         0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+29.0690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1668
_reflns_number_gt                4864
_reflns_number_total             5978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja068892bsi20070212_065042.cif
_cod_data_source_block           8mayfm
_cod_database_code               4109225
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ag1 Ag 0.25579(4) 0.27463(3) 1.98673(4) 0.01776(14) Uani 1 1 d .
Ag2 Ag 0.25506(4) 0.13029(3) 1.48661(4) 0.01807(14) Uani 1 1 d .
O1 O 0.5390(4) 0.2045(3) 1.3479(4) 0.0226(10) Uani 1 1 d .
O1' O 0.0700(4) 0.0941(3) 1.5985(4) 0.0191(9) Uani 1 1 d .
O2 O 0.4450(4) 0.0927(3) 1.3716(4) 0.0208(10) Uani 1 1 d .
O2' O -0.1153(4) 0.1036(3) 1.5423(4) 0.0226(10) Uani 1 1 d .
O3 O 0.6300(4) 0.1022(3) 1.4273(4) 0.0259(11) Uani 1 1 d .
O3' O -0.0264(4) 0.2034(3) 1.6290(4) 0.0233(10) Uani 1 1 d .
N1 N 0.1468(5) 0.2191(3) 1.0990(4) 0.0175(11) Uani 1 1 d .
N1' N 0.3671(5) 0.2259(3) 1.8717(4) 0.0164(10) Uani 1 1 d .
N10 N 0.5394(5) 0.1330(4) 1.3817(4) 0.0195(11) Uani 1 1 d .
N11 N 0.2436(5) 0.2824(4) 1.5055(5) 0.0242(13) Uani 1 1 d .
H11A H 0.2202 0.3048 1.4444 0.036 Uiso 1 1 calc R
H11B H 0.3137 0.3019 1.5295 0.036 Uiso 1 1 calc R
H11C H 0.1927 0.2946 1.5492 0.036 Uiso 1 1 calc R
N12 N -0.0246(4) 0.1337(4) 1.5906(4) 0.0178(11) Uani 1 1 d .
N3 N -0.0433(4) 0.1582(3) 1.1107(4) 0.0161(10) Uani 1 1 d .
N3' N 0.5584(5) 0.1684(4) 1.8597(4) 0.0197(11) Uani 1 1 d .
N6 N 0.3023(5) 0.2071(4) 1.2290(4) 0.0229(12) Uani 1 1 d .
H6A H 0.3459 0.2337 1.1917 0.027 Uiso 1 1 calc R
H6B H 0.3305 0.1901 1.2892 0.027 Uiso 1 1 calc R
N6' N 0.2150(5) 0.2173(4) 1.7403(4) 0.0205(12) Uani 1 1 d .
H6'1 H 0.1720 0.2449 1.7773 0.025 Uiso 1 1 calc R
H6'2 H 0.1869 0.2011 1.6798 0.025 Uiso 1 1 calc R
N7 N 0.1309(4) 0.1115(3) 1.3492(4) 0.0155(10) Uani 1 1 d .
N7' N 0.3853(5) 0.1195(3) 1.6219(4) 0.0170(11) Uani 1 1 d .
N9 N -0.0503(5) 0.0878(3) 1.2730(4) 0.0186(11) Uani 1 1 d .
N9' N 0.5683(5) 0.0982(3) 1.6981(4) 0.0173(10) Uani 1 1 d .
C2 C 0.0344(5) 0.2011(4) 1.0646(5) 0.0161(12) Uani 1 1 d .
H2 H 0.0073 0.2215 0.9997 0.019 Uiso 1 1 calc R
C2' C 0.4797(5) 0.2084(4) 1.9068(5) 0.0175(12) Uani 1 1 d .
H2' H 0.5054 0.2269 1.9730 0.021 Uiso 1 1 calc R
C4 C 0.0037(5) 0.1322(4) 1.2057(5) 0.0155(12) Uani 1 1 d .
C4' C 0.5133(6) 0.1420(4) 1.7655(5) 0.0191(13) Uani 1 1 d .
C5 C 0.1148(5) 0.1474(3) 1.2505(5) 0.0129(11) Uani 1 1 d .
C5' C 0.4014(5) 0.1560(4) 1.7196(5) 0.0132(11) Uani 1 1 d .
C6 C 0.1909(5) 0.1922(4) 1.1937(5) 0.0167(12) Uani 1 1 d .
C6' C 0.3237(5) 0.2000(4) 1.7763(5) 0.0153(11) Uani 1 1 d .
C8 C 0.0293(5) 0.0772(4) 1.3587(4) 0.0141(11) Uani 1 1 d .
H8 H 0.0134 0.0490 1.4172 0.017 Uiso 1 1 calc R
C8' C 0.4881(6) 0.0864(4) 1.6128(5) 0.0216(9) Uani 1 1 d .
H8' H 0.5045 0.0580 1.5546 0.026 Uiso 1 1 calc R
C11 C -0.1933(7) -0.0078(6) 1.1846(6) 0.038(2) Uani 1 1 d .
H11 H -0.1460 -0.0539 1.1947 0.045 Uiso 1 1 calc R
C11' C 0.7356(6) 0.0313(4) 1.8008(5) 0.0216(9) Uani 1 1 d .
H11' H 0.6914 -0.0116 1.8223 0.026 Uiso 1 1 calc R
C12 C -0.2748(7) -0.0069(6) 1.1033(7) 0.0398(15) Uani 1 1 d .
H12A H -0.3235 0.0384 1.0911 0.048 Uiso 1 1 calc R
H12B H -0.2830 -0.0514 1.0588 0.048 Uiso 1 1 calc R
C12' C 0.8335(8) 0.0509(7) 1.8568(7) 0.049(3) Uani 1 1 d .
H12C H 0.8788 0.0937 1.8365 0.059 Uiso 1 1 calc R
H12D H 0.8578 0.0221 1.9170 0.059 Uiso 1 1 calc R
C10' C 0.6926(5) 0.0751(4) 1.7043(5) 0.0210(13) Uani 1 1 d .
H10A H 0.7390 0.1242 1.6994 0.025 Uiso 1 1 calc R
H10B H 0.7036 0.0404 1.6460 0.025 Uiso 1 1 calc R
C10 C -0.1732(7) 0.0601(6) 1.2602(7) 0.0398(15) Uani 1 1 d .
H10C H -0.2235 0.1058 1.2372 0.048 Uiso 1 1 calc R
H10D H -0.1940 0.0421 1.3262 0.048 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 Ag1 N1' 135.24(19) 1_556 .
N1 Ag1 O2' 119.11(18) 1_556 4_666
N1' Ag1 O2' 96.18(17) . 4_666
N1 Ag1 O3 100.17(18) 1_556 4_566
N1' Ag1 O3 115.31(18) . 4_566
O2' Ag1 O3 76.10(15) 4_666 4_566
N7 Ag2 N7' 167.1(2) . .
N7 Ag2 N11 100.57(18) . .
N7' Ag2 N11 92.30(18) . .
N12 O2' Ag1 105.1(4) . 4_565
N10 O3 Ag1 103.9(4) . 4_665
C2 N1 C6 118.2(6) . .
C2 N1 Ag1 117.5(4) . 1_554
C6 N1 Ag1 123.6(4) . 1_554
C2' N1' C6' 118.6(5) . .
C2' N1' Ag1 116.8(4) . .
C6' N1' Ag1 123.5(4) . .
O3 N10 O1 121.0(6) . .
O3 N10 O2 120.0(6) . .
O1 N10 O2 119.0(5) . .
Ag2 N11 H11A 109.5 . .
Ag2 N11 H11B 109.5 . .
H11A N11 H11B 109.5 . .
Ag2 N11 H11C 109.5 . .
H11A N11 H11C 109.5 . .
H11B N11 H11C 109.5 . .
O3' N12 O2' 120.5(5) . .
O3' N12 O1' 119.5(5) . .
O2' N12 O1' 120.0(6) . .
C2 N3 C4 111.1(5) . .
C2' N3' C4' 111.8(5) . .
C6 N6 H6A 120.0 . .
C6 N6 H6B 120.0 . .
H6A N6 H6B 120.0 . .
C6' N6' H6'1 120.0 . .
C6' N6' H6'2 120.0 . .
H6'1 N6' H6'2 120.0 . .
C8 N7 C5 104.1(5) . .
C8 N7 Ag2 119.0(4) . .
C5 N7 Ag2 134.2(4) . .
C8' N7' C5' 103.6(5) . .
C8' N7' Ag2 119.8(4) . .
C5' N7' Ag2 134.8(4) . .
C4 N9 C8 106.5(5) . .
C4 N9 C10 127.0(6) . .
C8 N9 C10 126.4(6) . .
C4' N9' C8' 106.3(5) . .
C4' N9' C10' 129.0(5) . .
C8' N9' C10' 124.3(5) . .
N3 C2 N1 129.2(6) . .
N3 C2 H2 115.4 . .
N1 C2 H2 115.4 . .
N3' C2' N1' 128.8(6) . .
N3' C2' H2' 115.6 . .
N1' C2' H2' 115.6 . .
N9 C4 N3 126.8(6) . .
N9 C4 C5 107.5(5) . .
N3 C4 C5 125.7(6) . .
N3' C4' N9' 127.2(6) . .
N3' C4' C5' 125.7(6) . .
N9' C4' C5' 107.1(5) . .
C4 C5 N7 109.3(5) . .
C4 C5 C6 118.4(6) . .
N7 C5 C6 132.2(5) . .
C4' C5' N7' 109.9(5) . .
C4' C5' C6' 118.2(6) . .
N7' C5' C6' 131.8(5) . .
N6 C6 N1 119.8(6) . .
N6 C6 C5 122.9(6) . .
N1 C6 C5 117.3(5) . .
N6' C6' N1' 119.5(6) . .
N6' C6' C5' 123.7(6) . .
N1' C6' C5' 116.8(5) . .
N7 C8 N9 112.6(5) . .
N7 C8 H8 123.7 . .
N9 C8 H8 123.7 . .
N7' C8' N9' 113.1(6) . .
N7' C8' H8' 123.4 . .
N9' C8' H8' 123.4 . .
C12 C11 C10 124.1(9) . .
C12 C11 H11 117.9 . .
C10 C11 H11 117.9 . .
C12' C11' C10' 122.3(8) . .
C12' C11' H11' 118.8 . .
C10' C11' H11' 118.8 . .
C11 C12 H12A 120.0 . .
C11 C12 H12B 120.0 . .
H12A C12 H12B 120.0 . .
C11' C12' H12C 120.0 . .
C11' C12' H12D 120.0 . .
H12C C12' H12D 120.0 . .
N9' C10' C11' 113.1(6) . .
N9' C10' H10A 109.0 . .
C11' C10' H10A 109.0 . .
N9' C10' H10B 109.0 . .
C11' C10' H10B 109.0 . .
H10A C10' H10B 107.8 . .
N9 C10 C11 112.0(8) . .
N9 C10 H10C 109.2 . .
C11 C10 H10C 109.2 . .
N9 C10 H10D 109.2 . .
C11 C10 H10D 109.2 . .
H10C C10 H10D 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 N1 2.237(6) 1_556
Ag1 N1' 2.239(5) .
Ag1 O2' 2.537(5) 4_666
Ag1 O3 2.547(5) 4_566
Ag2 N7 2.179(5) .
Ag2 N7' 2.185(5) .
Ag2 N11 2.502(6) .
O1 N10 1.248(7) .
O1' N12 1.262(7) .
O2 N10 1.265(7) .
O2' N12 1.254(7) .
O2' Ag1 2.537(5) 4_565
O3 N10 1.246(7) .
O3 Ag1 2.547(5) 4_665
O3' N12 1.246(7) .
N1 C2 1.351(8) .
N1 C6 1.353(8) .
N1 Ag1 2.237(6) 1_554
N1' C2' 1.354(8) .
N1' C6' 1.353(8) .
N11 H11A 0.8900 .
N11 H11B 0.8900 .
N11 H11C 0.8900 .
N3 C2 1.337(8) .
N3 C4 1.362(8) .
N3' C2' 1.330(8) .
N3' C4' 1.349(8) .
N6 C6 1.334(8) .
N6 H6A 0.8600 .
N6 H6B 0.8600 .
N6' C6' 1.316(8) .
N6' H6'1 0.8600 .
N6' H6'2 0.8600 .
N7 C8 1.318(7) .
N7 C5 1.409(8) .
N7' C8' 1.321(8) .
N7' C5' 1.403(8) .
N9 C4 1.349(8) .
N9 C8 1.371(7) .
N9 C10 1.478(9) .
N9' C4' 1.351(8) .
N9' C8' 1.374(8) .
N9' C10' 1.475(8) .
C2 H2 0.9300 .
C2' H2' 0.9300 .
C4 C5 1.366(8) .
C4' C5' 1.374(8) .
C5 C6 1.420(8) .
C5' C6' 1.425(8) .
C8 H8 0.9300 .
C8' H8' 0.9300 .
C11 C12 1.330(11) .
C11 C10 1.485(13) .
C11 H11 0.9300 .
C11' C12' 1.309(11) .
C11' C10' 1.483(9) .
C11' H11' 0.9300 .
C12 H12A 0.9300 .
C12 H12B 0.9300 .
C12' H12C 0.9300 .
C12' H12D 0.9300 .
C10' H10A 0.9700 .
C10' H10B 0.9700 .
C10 H10C 0.9700 .
C10 H10D 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N6 H6B O2 0.86 2.26 2.989(7) 143.0
N6' H6'2 O1' 0.86 2.38 3.088(7) 140.2
